Triethylamine → Trans-(+)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-1H-indole-1-acetamide

HRID 542215

反応式

HRID 542215 の反応式
C(N(CC)CC)C.[N:8]1([CH2:17][C:18]([OH:20])=O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.ClC(OCC)=O.[CH3:27][NH:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>O1CCCC1>[CH3:27][N:28]([C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)[C:18](=[O:20])[CH2:17][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 904481H-Indole-1-acetic acidHCID 13377463Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-

生成物 1

HCID 18607177Trans-(+)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-1H-indole-1-acetamide収率 32%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Triethylamine (139 μl, 1 mmol) was added to a solution of 1H-indole-1-acetic acid (175 mg, 1 mmol) in tetrahydrofuran (10 ml) at -15° C. with vigorous stirring. Ethyl chloroformate (96 μl, 1 mmol) was added, and the mixture stirred for five minutes. A solution of trans-(±)-N-methyl-2-(1-pyrrolidinyl)cyclohexanamine (182 mg, 1 mmol) in tetrahydrofuran (2 ml) was added, and stirring continued for 30 minutes at -15° C., then 30 minutes at room temperature. The reaction was evaporated to small volume, the residue dissolved in ethyl acetate (50 ml), and washed with saturated sodium biocarbonate solution (3×50 ml). The organic extract was drige (MgSO4), evaporated under reduced pressure, and recrystallized from diethyl ether/methylene chloride to yield the amide (100 mg, 32%); Vmax C=0 1635 cm-1.

後処理

  1. stirringstirring
  2. waitcontinued for 30 minutes at -15° C.
  3. custom30 minutes
  4. customat room temperature
  5. customThe reaction was evaporated to small volume
  6. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  7. washwashed with saturated sodium biocarbonate solution (3×50 ml)
  8. extractionThe organic extract
  9. customevaporated under reduced pressure
  10. customrecrystallized from diethyl ether/methylene chloride

出典と根拠

ORDレコード
ord-b78c5c3004e445248105fe7e810969c9
出典データセット
uspto-grants-1987_04
特許番号
US04656182

関連ノート

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